Compounds having surface activity



Patented May 16, 1950 COMPOUNDS HAVING SURFACE ACTIVITY AND PROCESS FORPREPARING THEM Milton Kosmin, Los Angeles, Calif., assignor to MonsantoChemical Company, St. Louis, Mo., a

corporation of Delaware No Drawing. Application November 19, 1947,Serial No. 787,031

Claims.

The present invention relates to compounds having high surface activity,which compounds are materials of the polyglycol ether type.

It is known, according to the disclosure of U. S. Patent 1,970,578, thatstraight chain organic alcohols may be reacted with ethylene oxide toproduce polyglycol ethers. It is, furthermore, pointed out in the abovepatent that these materials may be used as surface active materials,including wetting out activity useful for treating textile products.After preparing and testing straight chain polyglycol ethers accordingto the prior known methods, I have found that these materials do notpossess a sufficiently high activity as wetting agents to make their usefor this purpose of commercial value.

I have now found, however, that if in place of the straight chainalcohols previously employed, I employ. 5-ethyl-nonanol-2 and condensethe same with ethylene oxide so that at least 5 moles, but less than 16moles, of ethylene oxide are combined as the polyglycol ether radical Iobtain a series of products exhibiting greatly improved wettingproperties in aqueous solution. The improvement manifests itselfthroughout the range of compositions produced from 5 moles of ethyleneoxide per mole of alcohol to and including moles of ethylene oxide permole of alcohol, the improvement commencing sharply when the compositioncontains 5 moles of condensed ethylene oxide per mole of alcohol andending sharply when 15 moles of ethylene oxide are condensed per mole ofalcohol.

The present compounds are believed to have the structural formulaindicated below:

where nis an integer having a value of from 3 to 13.

The improvement in surface activity possessed by the present compoundsmay be illustrated by comparing the speed of wetting as measured by thewell known Draves test upon aqueous solutions of the present and relatedmaterials. In the tabulation below is shown the speed of wetting inseconds as measured by the Braves test upon 0.5% water solutions of eachof the prod- 2 ucts described herein. Obviously, other suitableconcentrations may be employed.

For the purpose of comparison, data are presented in the abovetabulation showing the speed of wetting of closely related products.

The condensation products were produced according to the followingexamples:

Example 1 One gram mole of 5-ethyl nonanol-2 is placed in a containerand heated to 155 to 160 C. 0.2% solid KOH is added to the alcohol andthen a stream of gaseous ethylene oxide is passed into the heatedalcohol. The addition of ethylene oxide is condensed in this manneruntil a total of 5 moles, as determined by increase in weight, hascombined with the alcohol. The reaction is then stopped by'discontinuingthe flow of ethylene oxide and the product removed from the reactionvessel. The product is a yellow, low-melting solid, freely soluble inwater and exhibits exceedingly rapid wetting properties. When dissolvedin water in amounts sufficient to form 0.5% solution the solution soprepared possessed an instant wetting speed in the Braves test.

The product produced according to this example has the structuralformula:

cmomomomoncmomonom One gram mole of 5-ethyl nonancl-2 was heated at atemperature of to C. with ethylene oxide, as described in Example 1above. The addition of ethylene oxide was continued until a total of 10gram moles of ethylene oxide as determined by increase in weight hadcombined with the alcohol. The reaction was discontinued and the productremoved from the reaction vessel. The product was a yellow. low-meltingsolid, freely soluble in water and when dissolved in water to form a0.5% solution, the solution was found to possess an instant wettingspeed in the Draves test.

The product produced according to this example has the structuralformula:

CHrCHgCHgCHzCHCHsCHaOHCH;

Example 3 One gram mole of 5-ethyl nonanol-2 was condensed with ethyleneoxide in the same manner.

The above products may also be employed as emcient detergents for thewashing of soiled textile products. When so employed they may beutilized directly as produced in the above examples, or they maybe-combined with builders such as the various alkali metal salts,particularly the alkaline phosphates and employed in the built form.

whattclalmil: 1. Compounds having the formula: omomomomonomomoacm 1H:OIHI-(OIHIO)I|CIHCOH zvhile n is an integer having a value of from 3 2.A compound having the formula:

omomomomonomomonon,

" 2H; c,H.- o.H.o)=c1m0H 3. A compound having the formula:cmomomomorromomoncm 1H1 Cflr-(CaHaWaCIE 4. A compound having theformula: omomomomonomomonom 5. The process which comprises passingethylene oxide into 5-ethyl nonanol-2 until at least 5 moles and lessthan 16 moles of ethylene oxide have combined with each mole of said5-ethyl nonanol-2.

MILTON KOSMIN.

REFERENCES CITED The following references are of record in the file ofthis patent:

UNITED STATES PATENTS Number Name Date 2,316,842 Coleman Apr. 20, 19432,355,823 Schlegel Aug. 15, 1944 FOREIGN PATENTS Number Country Date584,367 Great Britain Jan. 14, 1947

1. COMPOUNDS HAVING THE FORMULA: